Paracetamol (acetaminophen; N-acetyl-p-aminophenol; APAP) is an analgesic and fever-reducing medicine:
It is an active ingredient in many widely sold over-the-counter medicines, such as Tylenol and Panadol. As a prescription pharmaceutical it is also sold in combination with opioid pain medications for treating more severe pain. It is the most commonly used medication for pain and fever in the United States. It is on the World Health Organizations List of Essential Medicines.
Introduced in the early 1900s, acetaminophen is a coal tar derivative that acts by interfering with the synthesis of prostaglandins and other substances necessary for the transmission of pain impulses. Although its action is similar to that of aspirin, it lacks aspirin's anti-inflammatory and blood-thinning effects, is less irritating to the stomach, and can be used by people who are allergic to aspirin. Heavy use has been linked to an increased incidence of liver failure, especially in alcoholic patients.
The original synthesis starts with phenol, which is nitrated with sodium nitrate to yield a mixture of ortho- and para-nitrophenol. These are then separated by distillation. The nitro group of the para-nitrophenol is then reduced to an amine, giving para-aminophenol. The amine is then acetylated with acetic anhydride:

An alternative industrial synthesis uses direct acylation of phenol with acetic anhydride. The resulting ketone is then converted to a ketoxime with hydroxylamine, followed by an acid-catalyzed Beckmann rearrangement to give the desired amide product:

In both approaches, the starting reactant, phenol, is derived from fossil fuels. There remains a long-felt and unmet need for a method to make paracetamol from a renewable feedstock.